LOCATION TO BOOK: With its unparalleled harbor views from the heated terrace (or a tent), the White Elephant exceeds all expectations. Bonus: Newlyweds can make their post-ceremony debut by taking a tugboat from a nearby launch to cocktail hour. “It’s really fun for all of the guests to see them arriving on water,” says Naylon.

Photograph by Istockphoto

MUST-HIRE VENDOR: The not-so-secret ingredient to a rocking reception? The Sultans of Swing, a popular cover band that has played for celebrities and local crowds alike. (You may recognize one of the band’s vocalists, Erika Van Pelt, who cracked the American Idol top 10 this year.)

GATHERING SPOT: For an intimate, al fresco rehearsal dinner, try the global menu at Fifty-Six Union or the modern dishes at American Seasons (pictured), both mainstays on the island.

Photograph by Dreamstime

GUEST EXCURSION: The NHA Whaling Museum is packed with Gray Lady history. Make sure friends and family get a chance to see the main attraction: a 46-foot sperm whale skeleton.

Photograph by Getty Images

SEASONAL SCOOP: Guests can explore the Coskata-Coatue Wildlife Refuge, specifically the lighthouse and long beaches of Great Point. All you need is a permit and a four-wheel drive vehicle with slightly deflated tires, which you can find at Affordable Rentals.